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ChemicalBook CAS DataBase List benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate
167757-46-2

benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate synthesis

6synthesis methods
-

Yield:167757-46-2 23%

Reaction Conditions:

with Lawessons reagent in tetrahydrofuran; for 4 h;

Steps:

4 Benzyl-4-carbamothioylpiperidine-1-carboxylate, cmpd. of formula 8 [R1=1-benzyloxycarbonyl-piperidin-4-yl]

Benzyl-4-carbamothioylpiperidine-1-carboxylate, cmpd. of formula 8 [R1=1-benzyloxycarbonyl-piperidin-4-yl]
Benzyl-4-carbamoylpiperidine-1-carboxylate (7.5 g, 38.6 mmol) was dissolved in THF (160 mL) and Lawesson's reagent (6.9 g, 17.1 mmol) was added.
After 4 h the solvent was evaporated and the residue purified by flash-chromatography on silica gel (DCM-MeOH 95/5) affording 1.8 g (23%) of the title compound, crystallized from MeOH.
HPLC: Rt: 5.28 min
1H NMR (600 MHz, DMSO-d6) δ ppm 9.40 (br. s., 1H), 9.11 (br. s., 1H), 7.42-7.24 (m, 5H), 5.07 (s, 2H), 4.07 (d, J=13.2 Hz, 2H), 2.90-2.73 (m, 2H), 2.69 (tt, J=3.8, 11.6 Hz, 1H), 1.70-1.64 (m, 2H), 1.64-1.55 (m, 2H)
HRMS (ESI) [M+H]+ calcd for C14H18O2N2S 279.1162. found 279.1163.

References:

US2013/324551,2013,A1 Location in patent:Paragraph 0318; 0319; 0320; 0321

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